Dating your roommates sister. People Who Married Or Dated Their Ex's Sibling Reveal How It Turned Out.



Dating your roommates sister

Dating your roommates sister

My roommate is stalking my sister. December 11, 5: A few months ago I started renting a room in a townhouse from a guy roughly my age mid 20s. He owns the place, so he's also my landlord. While chatting when I stopped by to drop off the security deposit, I mentioned that I had a sister living in the same area, and he started asking questions about her.

Politely, but as he showed me around the place, every pause in the conversation would be followed by, "So, when did your sister get out of school? I noticed it in retrospect after leaving that night, but didn't consider it a big deal and still wouldn't, if that was where it stopped. The next time I came over to move in, that conversational pattern was repeated, and when I noted that she was currently living with two female roommates herself, he made a point of mentioning multiple times that they were welcome to come over and hang out whenever they'd like, and when I note that my family will be stopping by in a few days, he asks if she'll be coming.

Still not a big deal. A few days later, she stops by with our parents, and he tries to talk her up, being a perfect gentleman with the single exception of making a point of drawing attention to how much money he makes. So now I've moved in, and two days later he says that he thought he saw my sister near where he works during lunch, which is completely impossible.

I actually don't see him that much, since his parents live in town and he spends a lot of nights at their place, which provides a pretext for him to email me asking me for emergency contact info, pointedly offering his brother's cellphone when he does. I give him mine, without any info for her. He also suggests that we go see a movie, and when I say that sounds good, he suggests that I invite my sister too. I note that she'll be out of town that weekend true , and he doesn't mention movies anymore.

For the next month, between him spending the night at his parents', and me spending more evenings out of the house, I don't see him much, though when I do he still asks how she's doing and keeps mentioning that she's welcome to do laundry here I'd stupidly mentioned that she was having problems with it at her place.

But I'd hoped that he'd finally got the hint that I don't want to set him up with her. Until yesterday, he mentions that he's located her on Facebook and has talked to her through it I don't use Facebook, so don't know exactly what that entails. I still wouldn't really worry about any of this, except that he started becoming obsessed with her before he met her, which squicks me out a little. He's a smart, hard working guy, and between his demanding, impressive IT job, online MBA courses and the time he spends with his parents his whole family moved here from China 10 years ago, so its a cultural thing , doesn't have much of a chance to go out and meet girls.

He seems like a nice, responsible guy, who has latched onto this as his best opportunity to get a girlfriend. I just instinctively always thought that its not really appropriate for guys to expect other guys to help them have sex with their sister. But who knows, they're both young adults, and who am I to interfere with their dating efforts? Should I help him set something up? Should I continue being neutral? Or should I yield to my gut and ask him to cut this out? I haven't mentioned any of this to my sister, and she's never mentioned or, until the Facebook incident, as far as I know, even noticed him.

Anonymous for their sake, not mine. I would mention to your sister what you've said here and let her decide whether she wants to get to know him. If she'd rather not, you can simply tell your roommate that your sister has a boyfriend and is usually busy. He seems to be obsessed with your sister for some reason maybe he thinks the only way he can meet a girl is through friends or family. It all seems very harmless at this point.

Is there any reason why you haven't told your sister about this yet? You should warn her about it so that she doesn't end up getting stuck in an awkward situation with the guy. Other than that this just seems like your average annoying roommate problem rather than anything you should be worried about.

Can you, in a really nice way, confront him? And be like "Hey dude, I'm super protective of my sister and I get a little weirded out when my friends pursue her. I need you to lighten up a bit. She's presumably an adult. Look at his expression and body language for cues. He'll probably look a bit deflated once he understands that you're not going to help him out.

Thanks, man, I knew you'd understand" and move on. If he brings it up again, throw your hands up and say: If she complains or asks about him, it is an entirely different situation, but until then, it seems best to limit your involvement. Do what she wants. I'm seconding the idea that while this guy is taking a pretty unusual approach to finding a girl to the point of being a bit disconcerting , this behaviour is not the same thing as stalking.

If it worries you then drop your sister a note saying that this guy seems to have gotten pretty focussed on the idea of meeting her just on the basis of her being your sister, and if she has any problems with him, then to let you know.

Beyond that, I'd let her make the decision for herself. Warn your sister that this man is obsessing about her. Tell him that her personal life is private.

Stop answering his questions about her. Move as soon as you can. In China, you would likely be involved with your family and possibly with fixing your sister up. However, your mother and your father's grandmother would have the final say in who your sister was allowed to be involved with. Check with your sister; does she like the guy?

Frankly, he has expressed a lot of interest in her, but its not technically stalking till he starts to call her all the time and "track" her. If she is into him, perhaps let it be. I would also invoke your mother's and paternal grandmother's authority in this just lay groundwork. If you really want him to back off say that your mother has already picked someone for your sister. The other issue is that he will likely be very sensitive to what his mother and paternal grandmother may think of him being involved with your sister.

They may be urging him to pursue it based on liking you and your family. Or they may not be aware. If you get an invitation to his family's house, accept it so you can suss out the situation. Go hop on facebook and you'll see what that entails. Basically you can send emails, and also post public messages to people. There isn't much else you can do. It sounds like he's not a total creep, just socially awkward IT job stereotype. Just get him to stop talking to you about it, but don't worry about your sister with this guy.

Sounds like she can handle herself. I don't see where this is interfering in your sister's romantic life. From the original post, it seems to be that she barely knows this guy exists, or cares. It does seem like this is interfering in your life, though -- his constant questioning and interest is making you uncomfortable.

Unfortunately, you have some culpability too: You answer his questions about her I agree that the guy seems harmless right now and clueless. I would go with a two-pronged approach: I don't know Facebook but I'm assuming it's like every other social networking site where she can just ignore him, or block him if he escalates.

You can drop both these into a pointed conversation without actually having to accuse him of an inappropriate interest. Lord knows you'll have the opportunity since he brings her up constantly.

You'll get folks here saying "You shouldn't have to lie! First of all, telling a white lie to a roommate in order to preserve the peace and make a weird living situation manageable is much more sensible than maintaining the highest level of principle at all costs by telling the whole truth, which is "I think you're stalking my sister and it's creeping me out" -- which could land the OP on the street.

And second of all, if a person in a position of authority over me seems to be making unwanted advances toward or harboring an unusual interest in a family member of mine, the last thing I'm going to do is tell that family member that it's her problem to solve, not mine. In a workplace, that would be sexual harassment -- why would we alter the standards in a private situation? I would handle it myself and try to keep the family member at arm's length, as long as she wasn't interested in the relationship.

Before getting too worried about it, maybe you should talk with your roommate about his expectations and what is culturally appropriate. From his standpoint, it might be that inquiring about your sister through you is the honorable approach, and that his intentions are all above board.

Clearly that's not appropriate in your setting or from your experience, but it may be an opportunity for mutual education. Anyhow, stop waiting for him to "get the hint. You might both be surprised. In all seriousness, a friend of mine is obsessed with my sister. It's awkward and he is always asking questions about her, and I just tell him to shut up and keep his obsession to himself. My feeling is that if anything did ever happen that's circumstances notwithstanding OK by me at least he has good taste?

You should just tell him you're not going to facilitate sex with your sister when you'd rather not think about it and like to pretend it never happens. He should understand that well enough. Alright, you need to consider the Chinese cultural aspect of this, in that what he is doing is considered perfectly acceptable over there, and as his friend you would be happy to help him out with this as it fits nicely within the concentric circles that make up Chinese society.

That being said he is a loser, presumably your sister is smart and will figure that out on her own without you accruing cockblocking karma. Just brush it off and ignore this unless he does something to upset her. If he keeps bringing it up just change the topic of conversation and talk about something else, as far as you are concerned around him your sister doesn't exist.

Remember there is no need to talk to either one of them unless he does something stupid which is unlikely because if he wasnt a pussy he would find girls on his own.

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Can I Date My Best Friend's Sister?



Dating your roommates sister

My roommate is stalking my sister. December 11, 5: A few months ago I started renting a room in a townhouse from a guy roughly my age mid 20s. He owns the place, so he's also my landlord. While chatting when I stopped by to drop off the security deposit, I mentioned that I had a sister living in the same area, and he started asking questions about her.

Politely, but as he showed me around the place, every pause in the conversation would be followed by, "So, when did your sister get out of school? I noticed it in retrospect after leaving that night, but didn't consider it a big deal and still wouldn't, if that was where it stopped. The next time I came over to move in, that conversational pattern was repeated, and when I noted that she was currently living with two female roommates herself, he made a point of mentioning multiple times that they were welcome to come over and hang out whenever they'd like, and when I note that my family will be stopping by in a few days, he asks if she'll be coming.

Still not a big deal. A few days later, she stops by with our parents, and he tries to talk her up, being a perfect gentleman with the single exception of making a point of drawing attention to how much money he makes.

So now I've moved in, and two days later he says that he thought he saw my sister near where he works during lunch, which is completely impossible. I actually don't see him that much, since his parents live in town and he spends a lot of nights at their place, which provides a pretext for him to email me asking me for emergency contact info, pointedly offering his brother's cellphone when he does.

I give him mine, without any info for her. He also suggests that we go see a movie, and when I say that sounds good, he suggests that I invite my sister too. I note that she'll be out of town that weekend true , and he doesn't mention movies anymore. For the next month, between him spending the night at his parents', and me spending more evenings out of the house, I don't see him much, though when I do he still asks how she's doing and keeps mentioning that she's welcome to do laundry here I'd stupidly mentioned that she was having problems with it at her place.

But I'd hoped that he'd finally got the hint that I don't want to set him up with her. Until yesterday, he mentions that he's located her on Facebook and has talked to her through it I don't use Facebook, so don't know exactly what that entails.

I still wouldn't really worry about any of this, except that he started becoming obsessed with her before he met her, which squicks me out a little.

He's a smart, hard working guy, and between his demanding, impressive IT job, online MBA courses and the time he spends with his parents his whole family moved here from China 10 years ago, so its a cultural thing , doesn't have much of a chance to go out and meet girls. He seems like a nice, responsible guy, who has latched onto this as his best opportunity to get a girlfriend. I just instinctively always thought that its not really appropriate for guys to expect other guys to help them have sex with their sister.

But who knows, they're both young adults, and who am I to interfere with their dating efforts? Should I help him set something up? Should I continue being neutral? Or should I yield to my gut and ask him to cut this out? I haven't mentioned any of this to my sister, and she's never mentioned or, until the Facebook incident, as far as I know, even noticed him.

Anonymous for their sake, not mine. I would mention to your sister what you've said here and let her decide whether she wants to get to know him. If she'd rather not, you can simply tell your roommate that your sister has a boyfriend and is usually busy. He seems to be obsessed with your sister for some reason maybe he thinks the only way he can meet a girl is through friends or family.

It all seems very harmless at this point. Is there any reason why you haven't told your sister about this yet? You should warn her about it so that she doesn't end up getting stuck in an awkward situation with the guy. Other than that this just seems like your average annoying roommate problem rather than anything you should be worried about.

Can you, in a really nice way, confront him? And be like "Hey dude, I'm super protective of my sister and I get a little weirded out when my friends pursue her. I need you to lighten up a bit. She's presumably an adult. Look at his expression and body language for cues. He'll probably look a bit deflated once he understands that you're not going to help him out. Thanks, man, I knew you'd understand" and move on.

If he brings it up again, throw your hands up and say: If she complains or asks about him, it is an entirely different situation, but until then, it seems best to limit your involvement. Do what she wants. I'm seconding the idea that while this guy is taking a pretty unusual approach to finding a girl to the point of being a bit disconcerting , this behaviour is not the same thing as stalking. If it worries you then drop your sister a note saying that this guy seems to have gotten pretty focussed on the idea of meeting her just on the basis of her being your sister, and if she has any problems with him, then to let you know.

Beyond that, I'd let her make the decision for herself. Warn your sister that this man is obsessing about her. Tell him that her personal life is private. Stop answering his questions about her. Move as soon as you can. In China, you would likely be involved with your family and possibly with fixing your sister up.

However, your mother and your father's grandmother would have the final say in who your sister was allowed to be involved with. Check with your sister; does she like the guy? Frankly, he has expressed a lot of interest in her, but its not technically stalking till he starts to call her all the time and "track" her. If she is into him, perhaps let it be.

I would also invoke your mother's and paternal grandmother's authority in this just lay groundwork. If you really want him to back off say that your mother has already picked someone for your sister. The other issue is that he will likely be very sensitive to what his mother and paternal grandmother may think of him being involved with your sister. They may be urging him to pursue it based on liking you and your family. Or they may not be aware. If you get an invitation to his family's house, accept it so you can suss out the situation.

Go hop on facebook and you'll see what that entails. Basically you can send emails, and also post public messages to people. There isn't much else you can do. It sounds like he's not a total creep, just socially awkward IT job stereotype. Just get him to stop talking to you about it, but don't worry about your sister with this guy.

Sounds like she can handle herself. I don't see where this is interfering in your sister's romantic life. From the original post, it seems to be that she barely knows this guy exists, or cares. It does seem like this is interfering in your life, though -- his constant questioning and interest is making you uncomfortable.

Unfortunately, you have some culpability too: You answer his questions about her I agree that the guy seems harmless right now and clueless. I would go with a two-pronged approach: I don't know Facebook but I'm assuming it's like every other social networking site where she can just ignore him, or block him if he escalates.

You can drop both these into a pointed conversation without actually having to accuse him of an inappropriate interest. Lord knows you'll have the opportunity since he brings her up constantly. You'll get folks here saying "You shouldn't have to lie! First of all, telling a white lie to a roommate in order to preserve the peace and make a weird living situation manageable is much more sensible than maintaining the highest level of principle at all costs by telling the whole truth, which is "I think you're stalking my sister and it's creeping me out" -- which could land the OP on the street.

And second of all, if a person in a position of authority over me seems to be making unwanted advances toward or harboring an unusual interest in a family member of mine, the last thing I'm going to do is tell that family member that it's her problem to solve, not mine. In a workplace, that would be sexual harassment -- why would we alter the standards in a private situation? I would handle it myself and try to keep the family member at arm's length, as long as she wasn't interested in the relationship.

Before getting too worried about it, maybe you should talk with your roommate about his expectations and what is culturally appropriate. From his standpoint, it might be that inquiring about your sister through you is the honorable approach, and that his intentions are all above board. Clearly that's not appropriate in your setting or from your experience, but it may be an opportunity for mutual education.

Anyhow, stop waiting for him to "get the hint. You might both be surprised. In all seriousness, a friend of mine is obsessed with my sister. It's awkward and he is always asking questions about her, and I just tell him to shut up and keep his obsession to himself.

My feeling is that if anything did ever happen that's circumstances notwithstanding OK by me at least he has good taste? You should just tell him you're not going to facilitate sex with your sister when you'd rather not think about it and like to pretend it never happens. He should understand that well enough. Alright, you need to consider the Chinese cultural aspect of this, in that what he is doing is considered perfectly acceptable over there, and as his friend you would be happy to help him out with this as it fits nicely within the concentric circles that make up Chinese society.

That being said he is a loser, presumably your sister is smart and will figure that out on her own without you accruing cockblocking karma. Just brush it off and ignore this unless he does something to upset her. If he keeps bringing it up just change the topic of conversation and talk about something else, as far as you are concerned around him your sister doesn't exist.

Remember there is no need to talk to either one of them unless he does something stupid which is unlikely because if he wasnt a pussy he would find girls on his own.

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5 Comments

  1. You may want to have a frank conversation about this with him, in which you explain politely that his constant discussion of your sister is bothering you, and that he should chill out. Frankly, he has expressed a lot of interest in her, but its not technically stalking till he starts to call her all the time and "track" her. I actually don't see him that much, since his parents live in town and he spends a lot of nights at their place, which provides a pretext for him to email me asking me for emergency contact info, pointedly offering his brother's cellphone when he does.

  2. If she'd rather not, you can simply tell your roommate that your sister has a boyfriend and is usually busy.

  3. It's awkward and he is always asking questions about her, and I just tell him to shut up and keep his obsession to himself.

  4. I noticed it in retrospect after leaving that night, but didn't consider it a big deal and still wouldn't, if that was where it stopped. There isn't much else you can do. We date a couple years, I start attending family events regularly.

  5. I'm seconding the idea that while this guy is taking a pretty unusual approach to finding a girl to the point of being a bit disconcerting , this behaviour is not the same thing as stalking. While chatting when I stopped by to drop off the security deposit, I mentioned that I had a sister living in the same area, and he started asking questions about her.

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